Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.

Patents

  1. Advanced Patent Search
Publication numberUS5171328 A
Publication typeGrant
Application numberUS 07/770,865
Publication dateDec 15, 1992
Filing dateOct 4, 1991
Priority dateOct 4, 1990
Fee statusLapsed
Also published asCA2052613A1, DE4031279A1, DE59101235D1, EP0479075A1, EP0479075B1
Publication number07770865, 770865, US 5171328 A, US 5171328A, US-A-5171328, US5171328 A, US5171328A
InventorsHubert Trauth, Christos Vamvakaris
Original AssigneeBasf Aktiengesellschaft
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Polypiperidinyl derivatives; light, oxygen and heat resistance
US 5171328 A
Abstract
Wood stains contain in addition to a colorant and a solvent at least one stabilizer against the action of light, oxygen and heat on the wood treated with the wood stain, said stabilizer containing at least one structural element of the formula I ##STR1## where X is oxygen or nitrogen.
Images(8)
Previous page
Next page
Claims(5)
We claim:
1. A wood stain containing in addition to a colorant and a solvent at least one stabilizer against the action of light, oxygen and hat on the wood which has been treated with the wood stain, said stabilizer containing at least on structural element of the formula I ##STR13## where X is oxygen or nitrogen, wherein the colorant is a solvent dye or an alcohol-soluble acid dye, in either case from the group of the azo or disazo dyes.
2. A wood stain as claimed in claim 1, wherein the stabilizer is
(a) a 4-formylaminopiperidine derivative of the formula Ia ##STR14## where n is 1 or 2,
R1 is hydrogen, C1 -C4 -alkyl, allyl, hydroxymethyl, β-hydroxyethyl, C1 -C4 -acyl, benzoyl or benzyl, and for n-1
Y is C1 -C18 -alkyl, which may be interrupted by from 1 to 4 nitrogen or oxygen atoms, C3 -C12 -cycloalkyl, phenyl, which may be C1 -C4 -alkyl-, fluorine-, chlorine-, bromine-, C1 -C4 -alkoxy-, methylenedioxy- or di-C1 -C4 -alkylamino-substituted, a radical of the formula ##STR15## or C7 -C12 -phenylalkyl which may be additionally substituted on the phenyl nucleus by C1 -C4 -alkyl, fluorine, chlorine, bromine, C1 -C4 -alkoxy, methylenedioxy or di-C1 -C4 -alkylamino, or for n=2
Y is C2 -C8 -alkylene, C5 -C18 -cycloalkylene, phenylene, C8 -C15 -phenylalkylene or C4 -C18 -alkylene which is interrupted by from 1 to 4 oxygen or nitrogen atoms, or
(b) a glycoluril derivative of the formula Ib ##STR16## where R2 and R3 are each hydrogen, C1 -C4 -alkyl, carbomethoxy, carboethoxy, benzyl or phenyl, or
(c) a mono- or dicarboxylic ester of the formula Ic or Id ##STR17## where R4 is C1 -C18 -alkyl which may be interrupted by from 1 to 4 nitrogen or oxygen atoms, C3 -C12 -cycloalkyl, phenyl which may be C1 -C4 -alkyl-, fluorine-, chlorine-, bromine-, C1 -C4 -alkoxy-, methylenedioxy- or di-C1 -C4 -alkylamino-substitute, or C7 -C12 -phenylalkyl which may be additionally substituted on the phenyl nucleus by C1 -C4 -alkyl, fluorine, chlorine, bromine, C1 -C4 -alkoxy, methylenedioxy or di-C1 -C4 -alkylamino,
R5 and R6 are each hydrogen, C1 -C4 -alkyl or C7 -C12 -phenylalkyl which may be additionally substituted on the phenyl moiety by C1 -C4 -alkyl, chlorine, bromine, hydroxyl or cyano, and
m is from 1 to 12, and compound Id may be in the form of a polymer.
3. A wood stain as claimed in claim 1, additionally containing one or more UV absorbers selected from the classes of the 2-(2'-hydroxyphenyl)benzotriazoles, 2-(2'-hydroxyphenyl)-1,3,5-triazines, 2-hydroxybenzophenones, imidazole-2-carboxanilides, oxalodiamides, acrylates which are phenyl- or hetaryl-substituted in the 3-position, and the heterocyclic amidine derivatives.
4. A wood stain as claimed in claim 1, containing the stabilizer alone or a mixture of stabilizers and UV absorbers selected from the classes of the 2-(2'-hydroxy-pheny1)benzotriazoles, 2-(2'-hydroxyphenyl)-1,3,5-triazines, 2-hydroxybenzophenones, imidazole-2-carboxanilides. oxalodiamides, acrylates which are pheny1- or hetary-substituted in the 3-position, and the heterocyclic amidine derivatives in an amount of from 0.05 to 10% by weight, based on the total amount of wood stain.
5. A mixture of stabilizers as set forth in claim 1 and UV absorbers selected from the classes of the 2-(2'-hydroxypheny)benzotriazoes, 2-(2'-hydroxyphenyl)-1,3,5-triazines, 2-hydroxybenzophenones, imidazole-2-carbox-anilides, oxalodiamides acrylates which are phenyl- or hetary-substituted in the 3-position and the heterocyclic amidine derivatives in a weight ratio of from 5:1 to 1:5 for stabilizing wood which has been treated with a wood stain against the action of light, oxygen and heat.
Description

The present invention relates to wood stains which in addition to a colorant and a solvent contain at least one stabilizer against the action of light, oxygen and heat on the wood which has been treated with the wood stain, said stabilizer containing at least one structural element of the formula I ##STR2## where X is oxygen or nitrogen.

For the purposes of the present invention wood stains are, in line with Ullmanns Encyklop/uml/a die der technischen Chemie, 4th edition, volume 12, page 681 (1), formulations of dyes and color pigments which ar present dissolved or suspended in an organic solvent, preferably an alcohol, and may contain small amounts of customary additives such as binders. They are used for treating, specifically coloring, wood.

The wood which has been treated with these wood stains is known to degrade or even disintegrate very rapidly under the action of light, oxygen and heat. As an outward sign of this degradation or disintegration, the colorant present in or on the surface of the wood will usually turn yellow or become discolored in some other way. Hitherto there has been no effective remedy.

It is an object of the present invention to provide stabilizers which will ensure satisfactory protection of the treated wood.

We have found that this object is achieved by the stabilizers with at least one structural element of the formula I defined at the beginning.

Polyalkylpiperidinyl groups of formula I are known as active moieties of ultraviolet absorbers and stabilizers for plastics and coatings, for example from EP-A-316 582 (2) and EP-A-213 570 (3). It is all the more surprising that such compounds, when used in wood stains, also show excellent stabilizing effects on the wood treated therewith.

The stabilizers with structural elements of the formula I which are usable according to the present invention are organic compounds which can also exist in oligomeric or polymeric form. They must have sufficient light, heat and storage stability and be sufficiently compatible with wood materials. They must also have a minimum level of solubility in the solvents used for wood

Particularly advantageous stabilizers are the following classes of substances:

(a) 4-formylaminopiperidine derivatives of the formula ##STR3## where n is 1 or 2,

R1 is hydrogen, C1 -C4 -alkyl, allyl, hydroxymethyl, β-hydroxyethyl, C1 -C4 -acyl, benzoyl or benzyl, and for n=1

Y is C1 -C18 -alkyl, which may be interrupted by from 1 to 4 nitrogen or oxygen atoms, C3 -C12 -cycloalkyl, phenyl, which may be C1 -C4 -alkyl-, fluorine-, chlorine-, bromine-, C1 -C4 -alkoxy-, methylenedioxy-or di-C1 -C4 -alkylamino-substituted, a radical of the formula ##STR4## or C7 -C12 -phenylalkyl which may be additionally substituted on the phenyl nucleus by C1 -C4 -alkyl, fluorine, chlorine, bromine, C1 -C4 -alkoxy, methylenedioxy or di-C1 -C4 -alkylamino, or for n =2

Y is C2 -C8 -alkylene, C5 -C18 -cycloalkylene, phenylene, C8 -C15 -phenylalkylene or C4 -C18 -alkylene which is interrupted by from 1 to 4 oxygen or nitrogen atoms, or

(b) glycoloril derivatives of the formula Ib ##STR5## where R2 and R3 are each hydrogen, C1 -C4 -alkyl, carbomethxy, carboethoxy, benzyl or phenyl, or

(c) mono- or dicarboxylic esters of the formula Ic or Id ##STR6## where R4 is C1 -C18 -alkyl which may be interrupted by from to 4 nitrogen or oxygen atoms, C3 -C12 -cycloalkyl, phenyl which may be C1 -C4 -alkyl-, fluorine-, chlorine-, bromine- C methylenedioxy- or di-C1 -C4 -alkylamino-substituted, or C7 -C12 -phenylalkyl which may be additionally substituted on the phenyl nucleus by C1 -C4 -alkyl, fluorine, chlorine, bromine, C1 -C4 -alkoxy, methylenedioxy or di-C1 -C4 -alkylamino,

R5 and R6 are each hydrogen, C1 -C4 -alkyl or C7 -C12 -phenylalkyl which may be additionally substituted on the phenyl moiety by C1 -C4 -alkyl, chlorine, bromine, hydroxyl or cyano, and

m is from 1 to 12, and compounds Id may be in the form of a polymer.

R1 is for example allyl, hydroxymethyl, β-hydroxyethyl, formyl, propionyl, butyryl, benzoyl, but in particular C1 -C4 -alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl or iso-butyl, and also acetyl and hydrogen. The most preferred meanings are hydrogen, methyl and acetyl.

C1 -C18 -alkyl Y is for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, n-pentyl, iso-pentyl, decyl, dodecyl, iso-tridecyl, tetradecyl, hexadecyl, octadecyl, pivalyl, 3,3-dimethyl-2-butyl, neopentyl, 4-methyl-2-pentyl and in particular n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, nonyl and iso-nonyl.

C2 -C18 -alkyl Y which is interrupted by from 1 to 4, preferably 1 or 2, ether oxygen or nitrogen atoms can be for example: --(CH2)3 N(CH3)2, --(CH2)3 N(C2 H5)2, --(CH2)3 --OCH3, --(CH2)3 --O--CH(CH3)2, --(CH2)2 O(CH2)2 --OH, --(CH2)4 --N(CH3)2, --(CH2)2 --N[CH(CH3)2 ]2, --(CH2) 2 --N--(C2 H5)2, --(CH2)2 N(CH3)2, --(CH2)2 --OCH3 and --(CH2)2 --OCH2 CH3.

Cycloalkyl Y is for example cyclopropyl, cyclobutyl, cyclopentyl, methylcyclohexyl, cycloheptyl, cyclooctyl, cyclododecyl or in particular cyclohexyl.

Examples of monosubstituted, disubstituted or trisubstituted phenyl Y are methoxyphenyl, toluene, xylene, trimethylphenyl, ethylphenyl, cumyl, fluorophenyl, chlorophenyl, bromophenyl, methylenedioxyphenyl and dimethylaminophenyl, the substituents being in the o-, m- or p-position.

C7 -C12 -phenylalkyl Y which may be additionally monosubstituted, disubstituted or trisubstituted on the phenyl nucleus is for example benzyl, methoxybenzyl, methylbenzyl, ethylbenzyl, isopropylbenzyl, tert-butyl-benzyl, trimethylbenzyl, fluorobenzyl, chlorobenzyl, bromobenzyl, methylenedioxybenzyl, β-phenylethyl, β-(tert-butylphenyl)ethyl, γ-phenylpropyl, β-(tert-butylphenyl)propyl, δ-phenylbutyl, ω-phenylhexyl or dimethylaminobenzyl, any substitutents on the phenyl nucleus being in the o-, m- or p-position.

C2 -C8 -alkylene Y and C5 -C18 -cycloalkylene Y can be for example: ##STR7## with p being from 2 to 8.

Of these, 1,2-ethylene, 1,3-propylene, 1,4-butylene and 1,6-hexamethylene are preferred.

Phenylene Y and C8 -C15 -phenylalkylene Y can be for example: ##STR8##

C4 -C18 -alkylene Y which is interrupted by from 1 to 4, preferably from 1 to 3, ether oxygen or nitrogen atoms can be for example: ##STR9##

If a stabilizer molecule contains a plurality of polyalkylpiperidinyl groups, the R1 moieties present therein may be identical or different.

R2 and R3 are each preferably ethyl, benzyl, phenyl, carbomethoxy, carboethoxy and in particular hydrogen and methyl.

R4 has the same meanings as the monovalent radical Y, except for the radical of the formula ##STR10##

Examples of R5 and R6 besides hydrogen are methyl, ethyl, n-propyl, n-butyl, benzyl, β-phenylethyl, p-methylbenzyl, p-chlorobenzyl, p-bromobenzyl, p-cyano-benzyl, p-hydroxybenzyl and 3,5-di-tert-butyl-4-hydroxy-benzyl; preference is given to n-butyl, 3,5-di-tert-butyl-4-hydroxybenzyl and in particular hydrogen.

The number m of unsubstituted or R5 - and R6 -substituted methylene bridge members in the dicarboxylic acid esters Id is preferably from 1 to 10, in particular from 1 to 8. If substituents are present, preferably only one carbon atom in the alkylene bridge is thus equipped; substituents may be present in particular when m is 1.

In a preferred embodiment, the wood stains additionally contain one or more UV absorbers selected from the classes of the 2-(2'-hydroxyphenyl)benzo-triazoles, 2-(2'-hydroxyphenyl)-1,3,5-triazines, 2-hydroxybenzophenones, imidazole-2-carboxanilides, oxalodiamides, acrylates which are phenyl- or hetaryl-substituted in the 3-position, and the heterocyclic amidine derivatives.

Specific examples of such UV absorbers are:

2-(2'-hydroxyphenyl)benzotriazoles the 5'-methyl, 3', 5'-di-tert-butyl, 5'-tert-butyl, 5'-(1",1",3",3"-tetramethylbutyl), 5-chloro-3',5'-di-tert-butyl- 5-chloro-3'-tert-butyl-5'-methyl, 3'-sec-butyl-5'-tert-butyl, 4'-octoxy, 3',5'-di-tert-amyl or 3',5'-bis-α,α-dimethylbenzyl derivative;

2-(2'-hydroxyphenyl)-1,3,5-triazines: 2,4,6-tris (2,-hydroxy-4'-octyloxyphenyl)-1,3,5-triazine, 2-(2'-hydroxy-4'-octyloxyphenyl)-4,6-bis(2',4'-di-methylphenyl)-1,3,5-triazine, 2-(2',4'-dihydroxy-phenyl)-4,6-bis(2',4'-dimethylphenyl)-1,3,5-tria-zine, 2,4-bis(2'-hydroxy-4'-propyloxyphenyl)-6-(2',4'-dimethylphenyl)-1,3,5-triazine, 2-(2'-hydroxy-4'-octyloxyphenyl)-4,6-bis(4'-methylphenyl)-1,3,5-triazine, 2-(2'-hydroxy-4'-dodecyloxyphenyl)-4,6-bis(2',4'-dimethylphenyl)-1,3,5-triazine; 2-hydroxybenzophenones: the 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 2,4,4'-trihydroxy or 2'-hydroxy-4,4'-dimethoxy derivative;

imidazole-2-carboxanilides: benzimidazole-2-carbox-anilides, such as the 4'-methoxy, 4'-ethoxy, 4'-propoxy, 4'-butoxy, 4'-methyl, 4'-ethyl, 4'-propyl or 4'-isopropyl derivative and the unsubstituted compound;

oxalodiamides: 4,4'-dioctyloxyoxanilide, 2,2'-di-octyloxy-5,5'-di-tert-butyloxanilide, 2,2'-di-dodecyloxy-5,5'-di-tert-butyloxanilide, 2-ethoxy-2-ethyloxanilide, N,N,-bis-(3-dimethylaminopropyl)-oxalamide, 2-ethoxy-5-tert-butyl-2-ethyloxanilide and its mixture with 2-ethoxy-2'-ethyl-5,4'-di-tert-butyloxanilide, mixtures of o- and p-methoxy- and also of o- and p-ethoxy-disubstituted oxanilides;

3-phenyl- or 3-hetaryl-substituted acrylates: ethyl or isooctyl o-cyano-β,β-diphenylacrylate, methyl α-carbomethoxycinnamate, methyl or butyl α-cyano-β-methyl-p-methoxycinnamate, methyl α-carbomethoxy-p-methoxycinnamate, N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline, 2-ethylhexyl 2-cyano-3,3-diphenylacrylate and 2-ethyl 2-cyano-3,3-diphenylacrylate;

heterocyclic amidine derivatives: compounds of the formulae ##STR11##

Imidazole-2-carboxanilides of the type mentioned are described in more detail in EP-A-284 828 (4) and heterocyclic amidine derivatives of the type mentioned are described in earlier German Patent Application P 39 16 494 (5).

Of these UV absorbers preference is given to compounds of the classes of the 2-(2'-hydroxyphenyl)-benzotriazoles and in particular the 2-hydroxybenzo-phenones and the imidazole-2-carboxanilides.

The wood stains of the present invention preferably contain as the colorant component a customary amount of a solvent dye or an alcohol-soluble acid dye which is chemically an azo or disazo dye. This dye can also be a metal complex dye. If acid groups are present, it may be in the form of an amine salt.

In general, the solvent and alcohol-soluble acid dyes are present in the wood stains in a state of complete or almost complete solution.

In addition, however, it is also possible to use other colorants such as disperse dyes or color pigments, provided the lower or complete absence of solubility of the colorant does not lead to technical problems with the application of the resulting suspensions.

Examples of highly suitable solvent dyes or alcohol-soluble acid dyes are the following azo or disazo dyes with their Colour Index designations: Solvent Yellow 82, 'Solvent Orange 54, Solvent Orange 56, Solvent Red 122, Solvent Red 160, Solvent Blue 70 and Acid Red 14.

The solvents used for the wood stains of the present invention are polar organic solvents such as carboxylic acids, eg. formic acid, acetic acid or propionic acid, including solid carboxylic acids, eg. oxalic acid or maleic acid, besides other solvents, esters, eg. ethyl acetate or methyl butyrate, ketones, eg. acetone or butanone, ethers, eg. ethylene glycol dimethyl ether, dioxane or tetrahydrofuran, carboxamides, eg. formamide or dimethylformamide, but in particular monohydric or polyhydric aliphatic alcohols which may additionally contain ether oxygen atoms, eg. methanol, ethanol, isopropanol, n-propanol, n-butanol, 1-methoxy-2-propanol, ethylene glycol, ethylene glycol monomethyl ether or diethylene glycol monomethyl ether, and mixtures thereof. Particular preference is given to ethanol, isopropanol and 1-methoxy-2-propanol and mixtures thereof. The polar solvent component may also include water, for example in a proportion of up to about 50% by weight, based on the solvent mixture, provided that a minimum level of solvent power for the colorant and, as the case may be, the stabilizer system is ensured.

The wood stains of the present invention contain the stabilizers described alone or a mixture of the stabilizers described and the abovementioned UV absorbers in an amount of from 0.05 to 10% by weight, preferably from 0.1 to 5% by weight, in particular from 0.2 to 2.5% by weight, based on the total amount of wood stain.

Suitable wood for treatment with the wood stains of the present invention comprises primarily shaped wooden articles with extended surfaces, for example boards, plywood and chipboard, which may be veneered, carved articles made of wood and for example furniture glued, nailed or screwed together from wooden components, but also wood in finely divided form, for example wood shavings or sawdust. Depending on the consistency and type of wood and the conditions under which it has been treated with the wood stain, the colorant can be directly on the surface of the wood material or be deep on the inside.

The wood stains of the present invention are applied to the wood in a conventional manner, for example by dipping the wood into baths of wood stain. The treatment time can be up to several hours, and the temperature of the wood stain baths ranges in general from about 20 to about 100° C., depending on the solvent system used.

After the treatment has ended, the wooden articles are in general air dried at room temperature; but it is also possible to employ more severe drying methods, for example elevated temperatures in a through-circulation cabinet.

The wood stains of the present invention can be used for treating any customary type of wood, eg. pine, spruce, fir, oak, ash, beech, maple, walnut, pearwood, teak, mahogany, chestnut, birch, larch, hazelnut, limewood, willow, poplar, elm, Scots pine, plane tree or aspen.

The present invention further provides a mixture of stabilizers having at least one polyalkylpiperidinyl group of the formula I and UV absorbers of the type mentioned in a weight ratio of from 5:1 to 1:5, preferably from 2:1 to 1:2, in particular 1:1, for stabilizing wood which has been treated with wood stains against the action of light, oxygen and heat.

This mixture is preferably added to the wood stains before the treatment of the wood, so that the stabilizer system can then be applied together with the colorant, ensuring uniform distribution of the stabilizer components with the colorant. However, the wood can also be brought into contact with the novel mixture of stabilizers and UV absorbers separately, advantageously in dissolved form, before or after treatment with the wood stain to bring about a layer distribution.

The wood stains of the present invention, in particular those which contain a mixture of the stabilizers described and UV absorbers, are highly suitable for permanently coloring wood of any consistency and grade. The wood thus treated is virtually immune to yellowing or discoloration, as is documented by appropriate light fastness measurements.

EXAMPLES

The wood stains used were prepared by the following method:

1 g of the dye indicated in the table was dissolved in a mixture of 630 g of ethanol and 185 g of 1-methoxy-2-propanol by gentle heating. The amounts of stabilizers and UV absorbers indicated in the table were then added at room temperature. Stabilizers and UV absorbers dissolved completely.

The following stabilizers (A to C) and UV absorbers (D to H) were used: ##STR12##

The wood was colored by the following method:

Commercial veneered boards of wood were dipped into a bath of wood stain and, to avoid evaporation losses, kept in a sealed vessel at 70-75° C. for 4 hours. The boards were then air dried at room temperature.

The colored boards were tested in the Suntest® accelerometer from Heraeus for 96 hours. Then the light fastness values of the colored wood surfaces were determined. The controls used were veneered wood boards treated in the same way with the corresponding wood stains but without stabilizers and UV absorbers and then exposed in the light fastness testing machine.

The light fastness indicates the degree to which the colorant changes on exposure to artificial light. The light fastness is rated on a scale from 1 to 8, with 1 denoting the worst performance and 8 the best performance. A light fastness rating of 8 indicates that the color strength of the colorant is unchanged, while a rating of 1 indicates that the colorant has been virtually completely destroyed.

The following table shows the results of the tests:

                                  TABLE__________________________________________________________________________Light fastness properties of colored veneered boards of wood                Concen-         LightExample  Stabilizer/         Amount tration         fastnessNo.    UV absorber         [g]    [% by wt.]                      Dye       rating__________________________________________________________________________ 1     A        2.5  0.3   Solvent Red 122                                3-4  2     A      5                1.2   Solvent Red 122                                4-5  D      5  3     A      10                2.4   Solvent Red 122                                5  F      10  4     A      5                1.2   Solvent Red 122                                4  G      5  5     A      5                1.2   Solvent Red 122                                3-4  H      5  6     B      5                1.2   Solvent Red 122                                5  D      5  7     B      5                1.2   Solvent Red 122                                4-5  F      5Comparison  --     --     --    Solvent Red 122                                1-2  8     A      10                2.4   Solvent Red 160                                4  F      10Comparison  --     --     --    Solvent Red 160                                1  9     A      10                2.4   Solvent Yellow 82                                3  F      10Comparison  --     --     --    Solvent Yellow 82                                1-2 10     A      10                2.4   Solvent Orange 54                                3-4  F      10Comparison  --     --     --    Solvent Orange 54                                2-3 11     A      10                2.4   Solvent Orange 56                                3  F      10 12     C      10                2.4   Solvent Orange 56                                3-4  E      10Comparison  --     --     --    Solvent Orange 56                                2  13    C      10                2.4   Solvent Blue 70                                2-3  E      10Comparison  --     --     --    Solvent Blue 70                                214     A      5      0.6   Acid Red 14                                3 15     A      5                1.2   Acid Red 14                                3-4  D      5 16     A      5                1.2   Acid Red 14                                3-4  G      5 17     A      5                1.2   Acid Red 14                                3-4  H      5 18     B      5                1.2   Acid Red 14                                3-4  D      5 19     B      5                1.2   Acid Red 14                                3-4  F      5Comparison  --     --     --    Acid Red 14                                1__________________________________________________________________________
Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2867493 *Jun 27, 1955Jan 6, 1959Chadeloid CorpActivation of wood for dyeing acid dyestuffs
US4648884 *Jul 17, 1985Mar 10, 1987Ciba-Geigy CorporationStorage stability
US4769457 *Aug 13, 1986Sep 6, 1988Basf AktiengesellschaftGlycoluril derivatives and their use as stabilizers for polymers
US4927925 *Oct 13, 1988May 22, 1990Ciba-Geigy CorporationPiperidine compounds and their use as thermal stabilizers
US4943391 *Dec 19, 1988Jul 24, 1990Basf AktiengesellschaftBicyclo(3.3.1)nonane derivatives and use in stabilizing organic materials
US4976889 *Nov 14, 1988Dec 11, 1990Basf AktiengesellschaftLight and heat stabilizers for plastics
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US5567206 *Jul 31, 1995Oct 22, 1996A.W. Faber-Castell Unternehmensverwaltung Gmbh & Co.Water based
US5746778 *May 23, 1996May 5, 1998A.W. Faber-Castell Unternehmensverwaltung Gmbh & Co.Water based stain for wood with dyes, stabilizers, buffers and complexing agents
US5942008 *Jun 11, 1997Aug 24, 1999Curto; CalogeroMethod of dyeing wood veneer at elevated temperatures and pressures
US6187387Mar 11, 1999Feb 13, 2001Ciba Specialty Chemicals CorporationStabilization of wood substrates
US6443996 *Apr 16, 1999Sep 3, 2002Maurice W. MihelichButyl salicylate and water solvent enabling soluble dye to penetrate into pores of such as granite, marble, limestone, and soapstone; resistant to removal or discoloration
US6545071Aug 14, 1997Apr 8, 2003Ciba Specialty Chemicals CorporationStabilizer mixtures
US6630002May 7, 2001Oct 7, 2003Ciba Specialty Chemicals CorporationProcess for the staining of wood with aqueous wood stains
US6645257 *Sep 15, 2000Nov 11, 2003Ciba Specialty Chemicals CorporationObtaining better penetration by treating with soluble pigment precursors under alkaline slightly conditions, acidifying with weak organic acid and thermally regenerating
US6653324Aug 24, 2000Nov 25, 2003Ciba Specialty Chemicals CorporationStabilization of wood substrates
US6737527 *Mar 28, 2001May 18, 2004Basf AktiengesellschaftIn particular for stabilizing plastics or coating materials; photostability
US6905520Aug 21, 2001Jun 14, 2005Stain, Inc.Mineral stains for wood and other substrates
US7019053Jan 21, 2003Mar 28, 2006Ciba Specialty Chemicals CorporationStabilizer mixtures
WO2005058565A1 *Dec 17, 2004Jun 30, 2005Fraunhofer Ges ForschungUse of benzotriazole derivatives for light-stabilizing wooden substrates
Classifications
U.S. Classification8/402, 8/568, 8/938, 8/681
International ClassificationB27K5/02, B27K3/34, C09D15/00, C08K5/34
Cooperative ClassificationY10S8/938, C09D15/00, B27K3/343, B27K5/02
European ClassificationC09D15/00
Legal Events
DateCodeEventDescription
Feb 20, 2001FPExpired due to failure to pay maintenance fee
Effective date: 20001215
Dec 17, 2000LAPSLapse for failure to pay maintenance fees
Jul 11, 2000REMIMaintenance fee reminder mailed
Jun 7, 1996FPAYFee payment
Year of fee payment: 4
Sep 11, 1992ASAssignment
Owner name: BASF AKTIENGESELLSCHAFT, GERMANY
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:TRAUTH, HUBERT;VAMVAKARIS, CHRISTOS;REEL/FRAME:006253/0491
Effective date: 19910918